How to Shop for the Perfect Date-Night Outfit

When it comes to jumping back into the dating pool, it can sometimes feel like you’re falling into the deep end, especially if you’ve just ended a long-term relationship. And if you have kids to think about as well, the idea of starting to date again could leave you fairly apprehensive. But once you’ve decided that you’re emotionally ready to take the leap and start looking for love (or at least companionship) again, you’re going to have to face an equally difficult task: deciding what to wear for your date. So when you’re out shopping for the perfect outfit, there are a few things you’ll want to keep in mind before you commit to making a purchase.

Here are some tips to help you select the right ensemble.

For starters, you need to seriously consider just what you want out of a date. Are you simply looking for something casual to help you get over your breakup? In that case you can’t go wrong with a slinky little dress that shows off all the exercise you’ve been doing since your previous partner left you high and dry. And don’t forget to pair it with some very tall pumps. On the other hand, you might be in the market for only serious relationship contenders. This means you’ll probably want to turn down the volume on your va-voom factor. It’s still nice to wear a dress (you want your date to know you’re a woman, after all), but forego the form-fitting variety that shows too much skin and opt instead for something classic and universally flattering, like a wide-strap V-neck that nips in at the waist and flares into an A-line skirt. Bring a wrap or cardigan to cover up a bit (or remove to reveal a bit if things are going well) and wear a cute pair of kitten heels for a shapely leg that isn’t quite as aggressive as a 5-inch stiletto.

Just for comparison, here are a few things you’ll want to avoid. You should never show up in a work outfit (even if it is a skirt suit). All you’re saying with this look is that you didn’t make the time to prepare for your date, or worse, you’re a workaholic. No guy wants to get wrapped up with a woman who cares more about her job than her personal life. Ditto on mommy clothes. If you arrive for your date in your tired old jeans, sneakers (or worse, Crocs), and a “comfortable” top, you may as well kiss your feminine appeal goodbye. No matter what you’re looking for in a man, you can be sure that he’s looking for a woman. So cast off the mantle of motherhood and career, just for an evening, and revel in the fact that you can be yourself for a while, without all the baggage.

The point is to not take dating too seriously. It’s not like the evening is going to end in a prenuptial agreement, so don’t overstress about selecting the perfect outfit. Just be yourself, look your best, and roll the dice. You’re going to have to ease back into the game, but you can definitely have some fun along the way and if nothing pans out, at least you’ve gotten a few new feel-good outfits out of the deal.